METHODS OF PRODUCING (CYCLOPENTYL[D]PYRIMIDIN-4-YL)PIPERAZINE COMPOUNDS Russian patent published in 2020 - IPC C07D405/04 C07D239/30 C07D239/52 

FIELD: chemistry.

SUBSTANCE: invention relates to an improved method of producing (S)-2-(4-chlorophenyl)-1-(4-((5R,7R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopent[d]pyrimidin-4-yl)piperazin-1-yl)-3-(isopropylamino)-propan-1-one corresponding to formula IX (ipatasertibu), which is an ACT inhibitor. Invention also relates to a method of producing an intermediate compound of formula I, as well as novel intermediate products for production thereof. Method of producing compound IX

IX

III

I,

where R² is hydrogen or an amino-protecting group, includes (i) reacting a compound of formula III or a salt thereof with a metalating agent, followed by addition of an aqueous acid to form a compound of formula I or a salt thereof; (ii) reducing a compound of formula I or a salt thereof to form a compound of formula VII_a

formula VII_a, or a salt thereof; formula VII_b (iii)

optional deprotection of a compound of formula VII_a or a salt thereof to form a compound of formula VII_b or a salt thereof and (iv) reacting a compound of formula VII_b or a salt thereof with a compound of formula VIII

formula VIII,

or a salt thereof to form a compound of formula IX or a salt thereof.

EFFECT: invention can be used in treating solid tumours, gastric cancer and prostate cancer.

35 cl, 7 ex